Novel synthetic spice based on alpha-ionone and preparation method of novel synthetic spice

A technology for ionone and synthetic fragrance, which is applied in the field of new synthetic fragrance based on ɑ-ionone and its preparation, and achieves the effects of environmental friendliness, high regio- and stereoselectivity, and convenient industrialization

Inactive Publication Date: 2018-06-08
ZHENGZHOU TOBACCO RES INST OF CNTC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, limited by the development of organic synthesis methodology, other new flavors derived from α-ionone are rarely reported.

Method used

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  • Novel synthetic spice based on alpha-ionone and preparation method of novel synthetic spice
  • Novel synthetic spice based on alpha-ionone and preparation method of novel synthetic spice
  • Novel synthetic spice based on alpha-ionone and preparation method of novel synthetic spice

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add ferric acetylacetonate (0.02 mmol) and ligand hexamethylphosphoric triamide (0.05 mmol) into the reaction tube, and add solvent toluene (5 ml) and α-ionone ( 0.5 mmol), placed in a temperature of 0°C, a solution of phenylmagnesium bromide (1 mmol) in ether was added dropwise to the reaction tube under stirring, and the reaction was continued at 0°C. After 4 hours, gas chromatography detected that the reaction was complete, and the reaction tube was returned to room temperature and cooled to zero, and saturated ammonium chloride solution was added dropwise to quench the reaction, and water was added after returning to room temperature. Extract with ether, wash the organic phase with 1% hydrochloric acid, saturated sodium bicarbonate and saturated brine successively, then dry with anhydrous sodium sulfate, filter, concentrate, and flash column chromatography to obtain 4-(2,6,6 - Trimethyl-2-cyclohexen-1-yl)-5-methyl-hexan-2-one, 75% yield, the product is a colorless l...

Embodiment 2

[0027] Add ferric chloride (0.02 mmol) and ligand triphenylphosphine (0.2 mmol) into the reaction tube, and add solvent diethyl ether (5 ml) and α-ionone (1 mmol ), placed at a temperature of -10 degrees, and added dropwise a solution of phenylmagnesium chloride (1 mmol) in tetrahydrofuran to the reaction tube under stirring, and kept at -10 degrees to continue the reaction. After 10 hours, gas chromatography detected that the reaction was complete, and the reaction tube was returned to room temperature and cooled to zero, and saturated ammonium chloride solution was added dropwise to quench the reaction, and water was added after returning to room temperature. Extract with ether, wash the organic phase with 1% hydrochloric acid, saturated sodium bicarbonate and saturated brine successively, then dry with anhydrous sodium sulfate, filter, concentrate, and flash column chromatography to obtain 4-(2,6,6 - Trimethyl-2-cyclohexen-1-yl)-5-hexen-2-one, yield 57%, product is colorles...

Embodiment 3

[0029] Add ferric chloride hexahydrate (0.02 mmol) and ligand trimethylchlorosilane (0.3 mmol) into the reaction tube, and add solvent tetrahydrofuran (15 ml) and α-ionone ( 1 mmol), placed at a temperature of 25 degrees, and a THF solution of phenylmagnesium bromide (1 mmol) was added dropwise to the reaction tube under stirring, and the reaction was continued at 25 degrees. After 2 hours, gas chromatography detected that the reaction was complete, and the reaction tube was returned to room temperature and cooled to zero, and saturated ammonium chloride solution was added dropwise to quench the reaction, and water was added after returning to room temperature. Extract with ether, wash the organic phase with 1% hydrochloric acid, saturated sodium bicarbonate and saturated brine successively, then dry with anhydrous sodium sulfate, filter, concentrate, and flash column chromatography to obtain 4-(2,6,6 - Trimethyl-2-cyclohexen-1-yl)-4-phenyl-hexan-2-one, 50% yield, the product ...

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Abstract

The invention discloses a novel synthetic spice based on alpha-ionone and a preparation method of the novel synthetic spice. The structure of the synthetic spice is shown as a formula 1 and a chemicalname of the synthetic spice is 4-(2,6,6-trimethyl-2-cyclohexene-1-yl)-4-phenyl-hexyl-2-one. The preparation method comprises the following steps: carrying out high-area and stereoselective 1,4-addition reaction on phenyl grignard reagent and alpha-ionone under catalysis of an iron catalyst, and then quenching an intermediate by saturated ammonium chloride to obtain the compounds. The preparationmethod has the advantages of simple operation, easily-obtained raw materials and reagent, capability of realizing reaction of a large steric hindrance substrate under mild conditions and better industrial application prospect. (The formula is shown in the description).

Description

technical field [0001] The invention belongs to the field of fragrance chemistry, and in particular relates to a novel synthetic fragrance based on α-ionone and a preparation method thereof. Background technique [0002] Compared with natural fragrances, synthetic fragrances have the advantages of definite ingredients, stable supply, and independent of seasons. Therefore, the development of synthetic fragrances has always been an important direction for the development of new fragrances in the flavor and fragrance industry. Starting from natural fragrance compounds, using organic synthesis to modify the structure and retain its main skeleton is a method to develop new fragrance compounds. For example, α-ionone has a powdery-sweet floral aroma characteristic of violet flowers, with a woody undertone, and is a very widely used natural fragrance (Xie Jianping. Tobacco Fragrance Raw Materials. Beijing: Chemical Industry Press, 2009). Some studies have found that starting from α...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/225C07C45/69C11B9/00
CPCC07C45/69C07C49/225C11B9/0061
Inventor 柴国璧孟庆华刘珊杨伟平范武席辉唐培培孙世豪
Owner ZHENGZHOU TOBACCO RES INST OF CNTC
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